Ammonium Chloride → 5-Chloro-2-[2-(2-methylphenyl)ethyl]-1H-benzimidazole-6-sulfonamide

HRID 904853Notes

Reaction equation

HRID 904853 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]#[N:11].[NH2:12][C:13]1[CH:19]=[C:18]([Cl:20])[C:17]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:16][C:14]=1N.[Cl-].[NH4+]>Cl>[Cl:20][C:18]1[C:17]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:16][C:14]2[NH:11][C:10]([CH2:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])=[N:12][C:13]=2[CH:19]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 132896884,5-Diamino-2-chlorobenzene-1-sulfonamideHCID 15164905HCID 15164905, compound

Product 1

HCID 132897155-Chloro-2-[2-(2-methylphenyl)ethyl]-1H-benzimidazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 11.5 g of 3-(2-methylphenyl)propionitrile in 50 ml of 6 N hydrochloric acid was added 11.8 g of 2-amino-4-chloro-5 sulfamylaniline and the suspension refluxed for 12 hours. The precipitate was collected by filtration and added with stirring to 200 ml of concentrated ammonium hydroxide. The free base was then collected and added to methanol; the methanol was brought to a boil, charcoal added, and the suspension filtered. Concentration in vacuo provided a semi-solid which upon treatment with acetonitrile gave a red solution and a precipitate (ammonium chloride). Concentration of the red solution in vacuo provided a solid which upon recrystallization from acetonitrile yielded off-white crystals, m.p. 205°-208°.

Workup

  1. temperaturethe suspension refluxed for 12 hours
  2. filtrationThe precipitate was collected by filtration
  3. additionadded
  4. customThe free base was then collected
  5. additionadded to methanol
  6. additionadded
  7. filtrationthe suspension filtered
  8. concentrationConcentration in vacuo
  9. customprovided a semi-solid which upon treatment with acetonitrile
  10. customgave a red solution
  11. customConcentration of the red solution in vacuo provided a solid which
  12. customupon recrystallization from acetonitrile yielded off-white crystals, m.p. 205°-208°

Sources & evidence

ORD record
ord-521dff4ae90d48439c237e6118ebfcbf
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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